


First times

by Villainous_hearts



Category: IT (2017), IT - Stephen King
Genre: ( ͡° ͜ʖ ͡°), 8000 words of smut, 8500 words of smut, Balloons, Bill Skarsgard - Freeform, Blood Kink, Blood Play, Claws, Cotton Candy, Drooling, Drug Use, Edging, F/M, Fear Play, Grinding, Hair Pulling, Hickies, I'm Going to Hell, IT - Freeform, Kinda, Kissing, Masterbation, Mentions of Rape, Oral Sex, Over, Powerplay, Purring, Quirofilia, Reader-Insert, Rough Sex, Scratching, Sexually Frustrated, Shapeshifting, She rides him, Smut, Stephen King - Freeform, Tendrils, Tentacles, Teratophilia, They dance, Voyeurism, Xenophilia, a little fluff at the end, and becomes relaxed, at the beginning, both consenting, both virgins, but - Freeform, but not in the fic, but not really, coulrophillia, cum slut, hated writing a 1000 word essay in school, he fucks her, just kidding, lip biting, neck biting, olfactory hallucination, pennywise - Freeform, porn with a plot, probably, she just takes something to help her sleep, strong swearing, that's also a thing, the longest smut I have written, they have sex twice, what I wrote in the hiatus of my actual book, yet here I am writing over 8500 words on porn, you'll float too
Language: English
Status: Completed
Published: 2019-08-25
Updated: 2019-08-25
Packaged: 2020-09-26 12:44:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,533
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20389906
Author URL: https://archiveofourown.org/users/Villainous_hearts/pseuds/Villainous_hearts
Summary: “you’re not going to eat me, are you?”There’s a moment of silence again and you know he’s contemplating it. This only encourages him as more fear wafts his way. He growls to himself. “Maybe.”“Or,” you began, “we could… I mean—I could teach you something. Something new. Something we could learn together.”It thought about this for it had previously been ignorant to its conflictions of fear onto others until it was forced to experience the same thing for itself. The unsuspecting emotion had originally bewildered it, having never felt anything but satisfaction from scaring and consuming others.To have its mind open to something again, was something it didn’t want to take its chances with, however, it couldn’t help but take a step back and ponder the possibilities of new experiences.A small growl emitted from where he stood—he was at war with himself. Entirely contradictory thoughts wracked its head. It didn’t know what to do.





	First times

**Author's Note:**

> Not my first time writing smut, but it is my first published work here. 
> 
> Omg, I was writing this until four in the morning and when I went to sleep, I had a dream that Pennywise was stalking me through the drains, (I could see his yellow eyes, the way Georgie did). That morning, my friend (who is terrified of clowns), said that she had a dream I was dating and wanted to introduce her to him—turned out to be Pennywise who gave her a balloon with a smile that stretched to its eyes. She passed out and woke up irl. The fucking coinkydink! 
> 
> Anyway, pardon me if it seems Pennywise is out of character, I really tried to make him seem as canon as possible.
> 
> I know I fucked up the pronouns in this (it/he), just makes it easier to read. 
> 
> Enjoy.

You slumped back on your bed, the previous week drilling into your head with deadlines from work and declined events from friends.

As you quickly climbed your way up in the workplace, more and more was demanded of you and you couldn’t help but be a people pleaser.

You sighed heavily, everything had taken its toll on you, not only mentally, but physically as well. You just used the remaining spites of energy relaxing in a hot bath with colourful water and thick mounds of bubbles. It was the only time you had to focus on yourself all week.

So, this is adulthood, unaware of neglecting yourself in exchange for a place in society with semi-decent pay.

You sighed again, thinking about how simpler times were when you were back in school. Then you chuckled to yourself out of spite, even back then, you had strived to please your tutors.

Your eyes were always on the prize—the prize being outstanding grades and recommendations. Of course, you had friends but relationships? You had those but nothing was ever serious. Even back then you were too focused on your work to be committed to a relationship let alone give a thought about yourself.

You rubbed your eyes with the open palms of your hands. Exhaustion didn’t scratch the surface. Tomorrow was your day off and you couldn’t help but schedule work into it rather than lounging on the sofa with a well-deserved show binge.

Too tired to sleep. Again, an understatement. You reached over to your bedside cabinet and pulled out some medication prescribed to prevent you from throwing up. You took these for those long business flights and drives but since they made you drowsy, you figured they would assist you to sleep.

You took one and laid back down, regretting your younger years. You had offers but you weren’t in the mind-set. But now, as you lay here, giving yourself permission to be selfish—or at least think about such selfish things, you couldn’t help but, well, regret.

You closed your eyes, remembering how paranoid work had somehow made you feel all week. That feeling, just simply _knowing_ someone was watching you would hit you like a brick wall. You would look around in retaliation, searching to find nothing out of the ordinary. And then the feeling was gone. Sometimes, the feeling felt as though it was following you.

It wasn’t the same as when a stranger watches you from a distance for an uncomfortably long amount of time only to avert their gaze sheepishly when you catch them, it was an eerie, gut-wrenching feeling. The instinctual red flag that tells you to run because something is going to go horribly wrong if you don’t and you only have seconds to do so.

That feeling had been following you but you dismissed it as some sort of mental fatigue courtesy of your work. Luckily, it wasn’t with you at the moment.

Then you began to notice the effects as the medicine began to work. It hadn’t hit you suddenly, but it was more noticeable as you shuffled in bed in an attempt to get comfy. Your muscles were slightly relaxed and your eyelids felt weighed upon.

You silently cursed at yourself as you realised that you were lying above your duvet instead of underneath it. You weren’t so relaxed that you couldn’t move, you were just incredibly fatigued and chose not to do anything about your current situation.

Besides, you weren’t sure if it was another side effect, a bad reaction or something that comes with being this tired but your whole body was now hyper-aware. This happened sometimes and now you remembered why you hadn’t taken more than the amount given in the packet,

You gently rubbed your eye, testing out the heightened sense of touch. You barely applied weight onto your closed eyelid when you noticed how soft your skin is and how more pressure made you want to coil back into your pillow.

Then you had an idea. Something you hadn’t done for a while.

You snaked a hand down to your thighs and began to slowly tease yourself by gliding the tips of your fingers gently over your sensitive skin. Then you moved up to your hips and stomach were your body quivered beneath its touch.

Then you found your nipple underneath your shirt and began circling the areola before lightly pinching it between your fingers and rolling it around. You arched your back slightly, already feeling a knot forming in your stomach as you cunt ached in negligence.

Your spare hand slipped into you night shorts where you began to pinch the needy nub, the feeling sent waves of electric to your abdomen immediately, tightening it the more you continued.

Your body was unable to tense the further you proceeded, which made it open to new, intense sensations. You gasped and arched into your own hands, your head lazily thrown back as you quickened your pace slightly. Your heart hammered violently against your chest.

Then it hit you. A smell.

It was as if somebody had snuck up to you and placed a plate of cotton candy directly under your nose.

You stopped and opened your eyes, reclining your head back from nothing but the smell. Not because it was horrible—it was anything but horrible, it was just a shock.

This was new, you had felt things more intensively but never had exhaustion or medication of any kind induce an olfactory hallucination.

Then the feeling came. That horrible feeling of being watched. You removed your hands and looked around the room, your breathing was incredibly heavy from previous excitement—and now, fear.

“No, no, no. Don’t stop now,” a voice spoke. You felt your body freeze in upmost horror and your eyes began to frantically search around your room as they had done during the week.

Your mouth became dry as your heart continued to quicken now, it felt as if it were trying to jump out and run away itself. Something, you couldn’t do thanks to the medicine you took. 

“Is this a hallucination too?” You whispered.

“I’m real. I’m real, I promise, you.” The voice, it wasn't recognizable. This only scared you more.

“If you’re real, then why can’t I see you?” You asked, sitting up onto your elbows and staring into the darkest corner of your room, the place where the voice was originating from.

“You wouldn’t want to see ol’ Pennywise. If you do, you won’t want to continue your little show, no you won’t.”

You furrowed your eyebrows at nothing. You had no intentions of continuing now, especially not after knowing you were and had been watched by someone. You lingered on the idea of this being inside your head, clinging onto this idea prevented you from freaking out entirely.

You slowly took a deep breath to steady your heart, “Pennywise, is that your name?”

“Why, yes. Yes, it is! I’m Pennywise, the dancing clown. What’s your name?”

“Why?”

“If I don’t know your name, we can’t be friends.”

You fell silent and thought about this. ‘_This is all in your head after all’_, you thought. But another thought asked, ‘_If that’s true, then why didn’t he know my name_?’ Then again, why would you want to be his friend? With a heavy sigh, you told him your name and you got a giddy giggle in response, “See? Was that so hard?”

“Why were you watching me?” You asked, ignoring his sarcastic question.

It took him a while to respond as if he were contemplating an answer, “Why?” the voice chuckled gleefully which caused your fear to surge through you once again, undoing the calmness you once had, “I’m curious, of course.” 

The figure watching you had two purposes in its life; sleeping and eating. It hadn’t had any other needs or requirements. It originally stalked you to figure out your fears and insecurities but tonight, you had confused it, stumped it even.

It knew about sex. It knew of it rather than from it. It was aware of violent acts of sex, how else would it have tormented its younger victims by taking on the form of their rapists and assaulters?

However, it didn’t understand it, didn’t understand the acts of self-pleasure or solely having sex for the fun of it. Especially having never experienced that himself.

Then they illuminated. A pair of orange eyes in the darkest corner of your room—exactly as you had suspected it to be. “Is that you?” You whispered, your heart beginning to race again.

“It is! It is, it is, it is!”

You stared at it as it stared back.

“Show me the rest of you, and I’ll continue,” you flushed with a shaky voice.

“_Promise_?”

You swallowed a lump that had formed in your throat, “yeah—promise.”

Then the figure revealed itself, [Honestly, I’m not gonna bore you with an info dump, y’all know what he looks like, it’s Bill Skarsgård as Pennywise).

He had his head lowered slightly which emphasized the dangerous glint in his apricot eyes. His expression was still and lethal.

You must have returned a horrified expression because he quickly beamed at you. But it was strange, his mouth showed a toothy grin but his eyes remained poisonous.

The knot in your abdomen tightened and a wave of shame washed over you. Not wanting to find out what would happen if you were to break your promise, you laid back down onto your back and hesitantly moved a trembling hand under your shorts.

You set a steady pace, strumming your clit and circling it, sending your nerves delicious shockwaves as you continued your unfinished session, your heart racing for many reasons. For a while, you refused to look anywhere that wasn’t his eyes and you couldn’t help but feel vulnerable under his perilous gaze, his eyes never leaving yours.

He was a great white shark; unpredictable and lethal, and you were the vulnerable otter in his waters. Not that he was contemplating eating you, just merely studying you, watching you. The wafts of fear didn’t help matters, it was like someone was constantly moving back and forth over a fan in his direction with freshly baked bread and cookies, or in his case; you.

When you felt comfortable enough, you closed your eyes and arched your neck, succumbing to the delectation of your heightened senses. It was as if your nerves had increased sensitivity and your body wasn’t strong enough to instinctively tense to your touch, causing your senses to go into overdrive instead of being dulled by them.

It was able to control his will-power, even as he stared at you with a thick line of saliva running from his bottom lip. A sight which you didn’t see as your exposed neck clenched from the attempts of wetting your throat with tight swallows.

He somewhat found this inviting but never acted upon it, his curiosity being the great motivator in holding him back. 

Normally, this whole situation would have freaked you out—especially if you weren’t hallucinating and you would have been too tense to lose yourself in the moment, but thanks to that miracle medicine, that wasn’t the case.

A shy moan escaped your mouth and you felt your face flush in embarrassment, you had never pleasured yourself in front of anyone like this and boy, was it intimidating.

At first, he thought you hurt yourself and grinned wider, noticing a light sheen of sweat on your exposed legs as you moved them lazily. Sure, you thought he smelled strongly of cotton candy, but to him, you were also enthralling. Especially your fear. 

“You smell delicious, such tasty, beautiful fear!” He spoke, making your eyes snap open and lock eyes with him. “You can smell my… my fear?”

“Oh yes and I can smell your sweat and your arousal too!”

“What does my sweat smell like?”

“Salty!”

“What about my… um, arousal?”

“_Sweet_,” his voice was low and it almost sounded like a growl rather than a word, causing a wave of excitement to flood through you momentarily.

“What does my fear smell like?”

“Oh, that’s a good question. Everyone’s fear smells different, yes? Some smell like old chimney smoke and barbeques whilst others smell like salty chips on a beach. But yours,” he pauses and you notice the line of saliva running past his plump bottom lip, “yours smell like freshly-baked bread and cookies. When you’re really scared, you start smelling like a sizzling slice of hot bacon.”

A few moments ago, it wouldn’t have considered eating you yet, but as he focused on those mouth-watering smells of yours, it knew it was only a matter of time before it lunged itself towards you as quick as a snake striking its prey.

Your movements become lazy as you slow down considerably, “Bacon?”

“That’s what I said, isn’t it? Yes, bacon! The way it sizzles in the pan and spits back the oil. Spit, spit!” He laughs, the slight movement causing the bells on his outfit to ring. 

Your hands cease movement and you become extremely self-aware, “you’re not going to eat me, are you?”

There’s a moment of silence again and you know he’s contemplating it. This only encourages him as more fear wafts his way. He growls to himself. “Maybe.”

You withdraw your hand to sit back up on your elbows, frustrated over the fact you had to stop again. “Or,” you began, “we could… I mean—I could teach you something. Something new. Something we could learn together.”

It thought about this for it had previously been ignorant to its conflictions of fear onto others until it was forced to experience the same thing for itself. The unsuspecting emotion had originally bewildered it, having never felt anything but satisfaction from scaring and consuming others.

To have its mind open to something again, was something it didn’t want to take its chances with, however, it couldn’t help but take a step back and ponder the possibilities of new experiences.

A small growl emitted from where he stood—he was at war with himself. Entirely contradictory thoughts wracked its head. It didn’t know what to do.

“It’s like a balloon,” you began, “an orgasm—I mean. Two bodies begin to—to engage in sexual acts and… and a knot begins to form in the abdomen—a build-up of tension, similar to a balloon being inflated. And it keeps going, getting bigger and bigger until it finally just… explodes. Only, it’s not as simple as ending after exploding, it’s like confetti disperses along with it and they flutter and glide in the air before gently resting on the floor. Like, coming down from the high.”

It watched you, repeating your words in its head and musing at the fitting analogy. It was always the one to lure others to it but it felt as if you were the one luring it for once. Glaring at the powerless situation he found himself in, he lunged towards you, somehow gliding across the room with his arms outstretched.

You flinched backwards and pulled your knees up to your chest in an attempt to further as much distance between you and it as possible.

It landed before you on your bed, its gloved hands gripping onto your exposed arms. The material was smooth but his grip was almost painful.

You whimpered and forced your eyes shut, fear paralysing you as you felt what you assumed to be its hair brush against your chin as it inhaled deeply.

“Such beautiful _fear_.”

A wave of exhilaration washed over you quickly followed by shame. Oh, how you began craving the weight of this being on top of you, to sink you into the mattress as it restrained you.

Your arms struggled against its grip but to no avail, if anything it forced your arms outwards so you couldn’t block him from smelling you further, taking your scent in deeper. Of course, your relaxed muscles weren't helping either, even at full strength, there was no way you could escape its grip.

It groaned in delight after inhaling deeply with its nose skimming your collar bone. You shivered at its touch. Fuck, you smelt good.

You opened your eyes and steadied your breathing, focusing on the slight pulsing of your skin as your heart hammered violently against your chest.

It noticed and reared its head slightly, locking its golden orbs with yours and smiling dangerously.

You leaned in and planted a quivering kiss on his lips.

It could have consumed you if it wanted to, nobody had ever voluntarily subjected themselves to kissing this monster let alone offer to fuck it to dispel any curiosities it may have had.

You were so enticing too, delicious food that looked and smelt divine—but wanted nothing more than to fuck it. How strange it would be if a piece of mouth-watering slab of salty meat began begging their consumer to stick their dick into them rather than eat them. That’s how alien the situation felt for it.

Luckily for you, it accepted the kiss curiously, knowing it could eat you anytime it wanted. Maybe it was humouring you for now.

It deepened the kiss, causing your teeth to click slightly. You drew in its plump bottom lip beneath your teeth and gave a gentle tug before pulling away.

When you pulled away, its expression had changed. What was once a venomous pair of eyes and a joyful grin had dropped to an intrigued and focused expression with a beautiful shade of blue eyes. Or perhaps its expression had relaxed and you were only seeing what you wanted to see, but that didn’t rule out the abnormal change in its eye colour.

Shock seized your voice momentarily but before you could query It, It began to slowly lean back in, so you decided to hold your tongue. However. It deliberately moved in at an agonizingly slow pace and you froze. Its ocean orbs settled on your lips and you nervously began to bite them.

The red tip of its nose finally grazed the side of yours as it drew in closer. Lips barely touching. A millimetre apart before it came to a pause.

Your lips quickly became hot with the air it dispelled until you were breathing him in and he was breathing you in. You quickly became dizzy and attempted to control your breathing as the warmth from his mouth seemed to have travelled straight to your groin.

Your breathing became heavy and unsteady the more you tried to control it. Fuck, you were feeling hazy, this whole thing was like a dream. A lucid dream where everything about you was hyper-aware, including your arousal.

The grip around your wrists relaxed, without granting you freedom. For a while, you believed he didn’t want you touching it, maybe it was uncomfortable with this kind of attention—where a human genuinely wanted to touch it. 

It didn’t take long until you were whimpering before him, begging him to kiss you. The desire for his mouth to dominate yours, to travel down to your neck. You squirmed like an impatient child, struggling against the gloved grip on your wrists only to be ignored completely.

You noticed it parting its lips ever so slightly, its eyes meeting yours;

“Psych.” 

It threw its head back and howled with a burst of joyous laughter, releasing your wrists to clap its hands once in a display of pure amusement.

Mortified, you hung your head to hide the red tint from your burning cheeks, only to have the being plant quick kisses all over your face in delight which made you shrink into yourself like an empty crisp packet on a bomb fire.

Fed up with the teasing endured already, you gathered all of the strength you could muster and in a sudden act of bravery to somehow spite him, you sat up on your knees and towered over him.

Noticing your sudden act of the confidence, it became silent and slowly cocked its head to the side expectantly, “Finally ready to play, are we?”

“Bite me.”

A knowing smirk tugged at its crimson lips but before it had a chance to reply, you straddled his waist and pulled your shirt over your head to reveal your breasts as it stared up at you.

However, it didn’t take long for your confidence to diminish as you realised Pennywise was the first person to see you naked—half-naked, exactly, but still. Quickly, you threw your arms around him, buried your face in the ruffles around its neck, your breasts pushed up against the soft material of his suit to cease the attention he gave you—the attention you demanded from him.

It condescended you with an ‘aww’ as he stroked your back gently with a gloved hand whilst his other rested on your thigh to steady you, “why is my pet suddenly so shy?” 

Ignoring him, your lips found the white of his neck. A portion of skin raised in between your teeth as you proceeded to create colourful hickies. He was the canvas to your paint; temporary colours of red plum and raspberry.

It trailed invisible, unpredictable lines around your naked back and you slowly began to rock your hips back and forth against his. Your clothed cunt sliding on its growing bulge.

The hand on your thigh tightened, possibly a warning, possibly a threat.

Your mouth left its neck with greedy sucking sounds and it groaned in a deep sinful voice. In fact, it was almost like a purr, rumbling in the back of its throat. You couldn’t help but groan lustfully against his now-flush skin.

The hand that held onto your thigh tightened until you could feel its fingernails beneath the glove—no, the nails were somehow on the outside now, as if they had grown and torn through the fabric within seconds. The nails dug into your skin and drew blood as easily as poking into a cooked tomato to reap the juices.

You hissed at the pain which ignited white, hot sparks of carnality and travelled straight to your cunt which was already damp and sticking to your shorts.

You felt the tickle of the red substance run down the curve of your thigh and drip onto your duvet.

The trailed hand on your back had reached your shoulder and pulled you in closer, pressing both of your bodies tighter together. Your lips travelled to the shell of his ear with his name on your lips. The distinctive, sweet smell of arousal and iron filled the radius around the two of you. 

Your throat became dry as the tension in your abdomen started to reach its tipping point.

You stopped rocking your hips with slow and heavy breathing, another edge to add to this evening. Your upcoming orgasm fading away like a dying flame. An impatient growl emitted from Penny, your hot pants of need on his ear wasn’t helping.

Your hand reached the crotch of its clothes in an attempt to locate the hem of its trousers, “Please.” You moaned before forcing yourself to swallow a lump of arousal in your dry throat.

“Since you asked so, very nicely,” it trailed as it reached inside of its pantaloons to pull out its cock.

You lowered your gaze curiously and froze, “what the—“A red tentacle sprung from the hem of his trousers and stood to attention. It wasn’t impossibly long to cause agonizing discomfort, but it held a nice girth and stood tall. Along the shaft of the cephalopod limb was occupied by many suction cups which were oozing with Penny's arousal.

“I-is this a joke?” You gasped, backing away to give him a look of disbelief.

Offended, it narrowed its eyes at you, “does it look like I’m joking, princess?”

“How… what are you?” You gaped, reaching out an experimental hand to the limb. You held onto it, sliding your thumb over a few of the suction cups to feel his arousal dampen your fingers. Penny groaned and bucked into your hand. It had the consistency of slime but was thin and clear like human semen. 

Your thumb travelled to your mouth where you curiously tasted him. You didn’t understand why you did this, it wasn’t as if you had anything to compare it to. At any rate, your tongue swirled around the pad of your thumb to collect the substance. An artificial taste of cotton candy settled on your taste buds and the texture was exactly how you’d assume it to be—slimy.

Your eyes hesitantly fell to your thigh where the piercing pain had remained. A gasped in shock left you when you saw that this entity didn’t have fingers but sharp talon-like claws instead and they were buried a few centimetres deep into your thigh.

Since the points of his claws hadn’t delved too deep into your flesh, you tried not to panic too much. The blood on the sheets were beginning to dry around the edges of each perfect circular splash and each indescribable shape. Your stomach flipped and you weren’t sure if you were going to be sick or slam him inside of you.

“I’ve always wondered about these,” he piped, the hand on your shoulder sliding down your collarbone and onto your breast, “sure is soft.” He giggled. You instinctively flinched from his touch, something that was ignored on his end. You thought about this and settled on him wanting to divert your attention away from what he was to what you were originally doing with him.

He flicked a nipple and chuckled to himself after you winced, repeating it a few times in amusement. Soon enough your nipple became erect and sensitive, each harsh flick of his gloved fingers were bolts of electricity to your groin which had you moaning.

“Oh so, this is an erogenous zone? How,” he flicks once more and you buck your hips, “interesting.” He laughs.

His gloved hand trailed to your shorts where he slid it to the side and made an intrigued sound as he eyed your wet cunt which was currently pulsing with arousal. This gloved hand, much to your appreciation, was still intact and when he removed the glove between his buck teeth, he revealed a pasty white hand with long, tapered fingers. It was as if his hands were from two different beings—like Frankenstein’s monster.

Now was his turn to experiment. Thanks to the slick juices of your arousal, his digit slid inside easily. You arched your back and groaned, your cunt finally being filled.

You weren’t sure if he did this to prepare you for that extra-terrestrial cock or because he was as curious as you were, but either way, you both relished the moment.

The pad of his thumb circled your clit lightly as he slid in another digit, the lewd squelching sounds returning as his pace quickly turned brutal to test your boundaries.

You threw back your head as your orgasm threatened to spill, causing your abdomen to heat up with a warning of ecstasy. His suit became bunched into your fists as you clung onto him for life before coming undone.

And then he stopped.

The orgasm faded once again but the tension and frustration remained. When coming back from the pre-high you noticed your heart was crashing and your breathing had once again escalated. Although it wasn’t something you had noticed, your body heat was through the roof, as bad as an all-over fever.

You flashed a glare his way only to be grinned at in response.

You pushed his hand away so that you could position yourself above him. The both of you locked eyes as you slowly eased him into you, causing you to gasp sensually and the claws in your thigh to tense and dig into your flesh some more.

You embraced him with breasts pressed once again against his clothes, you squeezed his waist with your thighs with what little strength you had and moaned languidly against his bruised neck.

Penny’s lips lowered onto your neck when he reached halfway inside and grazed his teeth along the delicate skin of your neck. He held himself back from ripping your throat out and feasting on you entirely; he already had you after all, and it was certainly the closest he’s ever been with a human or anything at all. He didn’t. Not with you. Not now. Things were getting interesting. 

The tentacle which was now deep inside of you began twitching and pulsing as you took the rest of him in, the slimy suction cups sucking you from every angle, it was how you’d imagine having the end of a snake explore you, instead of the mundane twitching of a human cock.

Penny growled to himself and purred deeply. Not even the purr sounded like anything you had ever heard.

His breath bounced off your skin causing you to shiver beneath him, you could feel the satisfaction he received from that small reaction as he smirked against your skin. Elongated, pale fingers entwined into your hair before harshly reaching for a fistful and pulling your head back to expose more of your neck to him.

You felt more of his teeth graze your skin, literally more, as if he had grown thousands of teeth which came to very fine points.

Your heart raced knowing if you jolted the wrong way, his teeth could easily puncture you. If that were to happen, what would stop him from ripping out and eating your trachea? That’s when it hit you; one thing that you know to be absolute is the fact that this thing defiantly gets off from fear, which explained the need to give empty threats.

The tip wavered impatiently which tickled your cervix, the girth stretching you wider than necessary. A sound that you hadn’t heard leave your mouth before erupted. It was lustful and came from the core of your need.

You began to squirm, bouncing yourself slightly along his tentacle, causing the bells on his suit to ring gently. The movement encouraged the suction cups to rub and constrict multiple areas deep inside your cunt, which only encouraged its lubrication. The bucking of your hips created noises similar to heavy boots running across a waterlogged bank after a torrential downpour.

As you stared up at the ceiling helplessly with your mouth slightly agape, you felt the serrated tips of its teeth graze your nipple. You gasped and tried to lower your gaze but the hand in your hair tightened possessively.

Not knowing which erected bud to toy with next, its tongue darted out. Purely experimental on its behalf as the skin's texture appeared different and slightly rougher compared to the rest of the skin. You arched your back, forcing it to take more of you in its mouth. White-hot pain travelled to your cunt when the teeth clamped down around your nipple, you yelped and flinched backwards.

You heard a twisted version of the giddy laugh from before, it was darker and sadistic. Appreciation for your subconscious invitation.

The long fingers which was once tangled in your hair slowly released and so you took the opportunity to take in his expression.

A cold shiver ran down your spine when you saw his eyes had returned to that wicked, feline glow of yellow. Your eyes quickly dropped to his mouth whilst he was in the process of shifting his form back to that of a normal set and his distinctive leporid front.

Despite witnessing the horror and feeling the sweat on your skin turn cold, your hips continued to bounce, your breasts jiggling slightly from the constant impact. 

Quickly, your legs grew tired as the energy you mustered to fuck him was beginning to wear thin. You slowed down and the squelching of his cock in your cunt became less frequent and sloppy. You held his gaze and slumped your shoulders, whining in frustration with the hopes of him taking the hint and chipping in soon. His only response was to condescendingly mimic you.

Exhausted, your haphazard bucking became slow and rigid. Slow and heavy pants filled the silence with an occasional sensual moan. Penny, on the other hand, was purring like an amplified zoo animal, you could feel his chest vibrating with low rumbles as he held his naked hand at the small of your back in an attempt to push more of himself into you.

The knot in your abdomen tightened until all was left was a small dot in the rope, you were on the edge and he knew it. You arched your back and craned you head as tension began to build on a mountain of what was already there.

In the heat of the moment, you reached for the wound (which was still occupied by his talons) to harvest the warm blood onto your fingers and smeared them sloppily onto your lips. A carnal gaze filtered his eyes as he began drooling, the saliva pooling onto your breasts.

“Kiss me, I promise I taste good,” you blushed, in an attempt to appear more seductive to him.

He crashed his lips against yours, striking like an aggravated snake and sucking the blood from your lips. The blood rushed and your lips swelled in no time. He kissed you greedily, hungrily and with no shame. You moaned in his mouth when your sensitive lips were harshly sucked on and he drew your bottom lip in-between his teeth before giving a painful tug.

The pain shot into your core and it was enough to spill out your orgasm. You cried out, bucking your hips to ride out an earth-shattering climax. Your whole body tensed around him as pure ecstasy flooded your senses. Your vision went white and of all the times you touched yourself, _never_ had you felt this good. Fuck, to feel something like this again, you would give a finger.

As your walls tightened around him, it triggered Penny’s release and, like lightning, he immediately latched onto your shoulder. Hundreds of sharp teeth pierced your skin accompanied with a thick line of saliva which trickled down your back.

Instead of feeling, what you would expect to be the fountain of cum squirt inside of you, you felt each suction cup filled with his slimy lubricant expel rapidly around your walls, like a 360° shower head, reaching all the right spots.

As for the teeth ingrained in your muscle, you were still high on your climax—still riding it out. The most you did was call out, a mix of a groan and a scream and continued to grind your hips in small circles. The pain was welcome—amplifying your climax.

For the first time, he didn’t mean it. He didn’t mean to bite you—it was an immediate reaction on his behalf. Having never orgasmed before, it became extremely perplexed and clung onto you upon instinct. 

When you both came back down from your high, you both remained intertwined within each other like mating slugs whilst panting for air.

Penny slowly released the hold he had on you with his teeth, causing you to wince. Blood quickly trickled down your arm and back, replacing the drool that had done the same thing. You both pulled back slightly to hold each other's gaze, his tentacle cock still inside you, pulsing, twitching, syncing with the heavy beat of your own heart.

“A-Are you okay?” You asked, face flushed. For a while, he stared at you as if he had just woken up from an episode of amnesia and couldn’t remember what had just happened. “That was…” he smirked, “fun. I have an idea! Let’s do that again, hm? But this time,” he lifted you off him, the tentacle audibly sliding out of you and pushed you onto your back where he removed his clothing, “_I’m in charge_.”

You were completely mixed about this because you were exhausted, on one hand, having just done the majority of the work and the sedative didn’t exactly help. If you were to walk now, your limbs would drag behind you. However, you were curious as to what was in store.

You laid before him, naked apart from the night shorts which were slanted to the side. Your entire body glistened with sweat, the holes in your thighs were highlighted in a deep red which trailed down the curve of your leg, your mouth was slightly smeared with blood and your punctured shoulder was beginning clot.

You stared up at him as he towered over you with a doe-eyed expression. Your intimidation reflecting on your face.

Fuck, he needed you badly. Poor bastard couldn’t help but drool over you—literally.

Penny lowered his mouth to your shorts where he nibbled at the material in the attempt to take them off, sometimes catching your skin between his teeth in the process.

When they were out of the way, he made a point about throwing the item of clothing over his head as if it was utterly useless, doing so in a melodramatic fashion. You stifled a small giggle, biting your lips as you eyed him.

His expression became serious again as he eyed your now-naked form. Completely exposed and completely vulnerable to him. A famous Jekyll and Hyde moment on his part.

Head lowered; yellow eyes glowed without illuminating more of his facial features. The red lines on his face were the next noticeable thing but barely. That look alone awakened new arousal and for some reason, you found yourself scooting backwards, only to have him reach for your ankles and yank you closer towards him. You slid down the mattress until he towered over you.

With his hands still gripping your ankles, he spread out your legs and positioned himself before you, easing into you once again. You melted into his touch, adoring being whole once again. Instantly, he began slamming into you whilst hooking an ankle over his shoulder. His large form appearing as if he could easily crush you if he wished.

The claps of skin slamming against skin, along with a few breathy moans from you and a low purr from him had filled the silence. Your breasts bounced with each thrust and drool pooled from the corner of your mouth. You grabbed fistfuls of the duvet to steady yourself, the headboard crashing repetitively against the wall.

Pen angled himself to the side as if to stretch out a tense muscle, only to have another set of arms protrude suddenly from underneath the first set.

You attempted to back away again, unhooking the ankle over his shoulder only to have it put back in place impatiently. The hand gripping your other ankle was brought up to his face where he threateningly nibbled at the skin. With his new set of hands, he grabbed onto your hip with one to bruise with an iron grip—careful this time not to use his talons and the other hand focused on your nipple where he pinched, twisted and pulled lightly.

You mewled, withering beneath him and arching into his touch.

His tongue spilled out from his mouth along with a thick line of drool in its wake and he gave your cheek a long, lick. His hips bucked violently as he pulled out almost all the way before slamming himself back inside to hit your cervix on each thrust. A tendril appeared behind him like a tail, _the tail of a devil_, you thought, and let your mouth hang open silently as it began to circle the bundle of nerves that had collected.

The knot in your stomach was incredibly tight, tighter than it had been all night. You knew it wasn’t going to belong until you came undone once again. With each thrust, you felt yourself being pushed backwards slightly until your head was just about touching the headboard, the fistfuls of duvet underneath your sweaty balled up fists were futile. 

“I-I’m gonna… I think I’m gonna c-come again. P-P-Pennywise,” you mewled between hits. Your clit was squeezed, pulled and palmed by his tendril as he experimented with your reaction and assisting you climax. 

“Go on then, my pet. Come. Come and then I’ll be able to eat you,” he slowly inched his face close towards yours before pretending to bite, causing you to flinch into the mattress. He smirked at your response and purred in pleasure, the vibrations tickling the skin of your legs and traveling through your body.

Two tendrils shot out from his back and clung onto the headboard to stop himself from literally banging you against the slab of wood. The wall took the beating instead and paint was quick to chip away at the severity from each thrust of his hips.

You were so close, you could practically taste it. Your mouth and throat were dry, your cunt was taking a vicious beating, both ankles were held in place, an extra hand had no doubt—bruised your hip, whilst the other one began playing with the neglected breast.

Fuck, you were close. And so was he.

However, something caught your eye behind Pen making you jump. A single red balloon bobbed by the bed next to you as if someone who wasn’t there had brought it up to you. You stared at it and the shine it gave from the moonlight reflecting off it.

You brought your attention back to penny who gave you his signature grin and that’s all you needed to come undone. Your high peaked as each nerve lit up and the knot released like a tourniquet snapping off the skin. Your vision went white and you arched your back, your body becoming rigid and toes curling. A series of curse words and his name spilled inaudibly from your mouth as you felt as high as a balloon in the wind.

As your cunt contracted and squeezed him, it triggered his release once again and he expelled into you, his warm cum. He squeezed your breast and hip painfully hard as he held himself back from dangerously biting you again, but that didn’t stop him from bearing you his sharp teeth, eyes now a deep red as anger and heat flared through his self-control. He growled—roaring almost, as the tendrils gripping the headboard chipped the wood beneath his grip.

The balloon popped, taking you back to reality and when your head snapped to face the space where the balloon had been, all that was left were confetti fluttering around the air before gently resting upon the ground. “Clever,” you breathed, noting the use of referencing.

The extra hand and tendrils retreated until he was back to normal again—normal for it at least and he pulled out of you, spilling more cum on the sheets. There was a lot of it and you couldn’t help but turn your nose up at it. It looked as if someone had spilled an entire cup of yogurt on the bed-, _and that was used to fill me up_, you thought shyly. 

When you caught your breathing enough to speak you looked at Penny who has dressed once again in his clown attire. You furrowed your eyebrows at him in wonder before sitting up yourself only to have his hand push you back down. “You do realise we can stop now, right?”

“I need to taste you.”

“A-are you going to… to eat me?”

You sat upon you elbows, ready to at least try to make a run for it.

“If you’re still, I’ll give you a balloon,” he promised, voice low.

You waited curiously, wondering if he was going to eat you and _how_ exactly he would do that. As you stilled, he assumed you to be complying and shifted himself between your legs. Embarrassed, you scooted back and squeezed your thighs shut, “W-what do you think you’re doing?”

Without answering, his talons ripped through both gloves again and threateningly poked the skin between your thighs as he pushed them apart. The crazy mass of his auburn mane tickled your inner thigs, wispy and soft flecks of hair causing you to shiver before him. 

First, he inhaled deeply and hummed appreciatively. Your skin pulsated with an accelerating heat, each pore seeming as though they were merely pulsating sweat with every beat.

You could feel the skin around your hairline prick, knowing fully well it was the discomfort of sweat but not knowing for sure if it was due to fucking each other or him being in a very personal area, ‘_Yeah, because fucking each other, drooling on me and smearing me in blood isn’t personal enough’, _You mentally hissed.

Your thoughts were interrupted when you felt the cold tip of his crimson nose press up against your clit as his tongue slid up and down your folds. The warmth of his breath hit your sex and you breathed a sigh of relief and mentally shook your head at yourself for thinking he was going to eat you.

Your body moved of its own accord when his tongue brushed teasingly against your overly-sensitive bud. His tongue was long and almost came to a point with plenty of his saliva coating it. It wasn’t very often when his tongue flicked your bud, in fact, you assumed it was an accident on his behalf. But whenever he did, your hips would violently jerk away from him.

He continued to tease you like this for a while until you reached for the tuff of his hair and gave a gentle tug. He chuckled against your skin, the vibrations against your clit caused the bundle of nerves to beg for friction the knot in your abdomen to reappear.

Noticing the milky substance of cum lingering on your cunt, Penny wrapped his painted lips around yours and proceeded to suck it off. “You taste as good as you smell,” he growled sinfully. “That… oh god, Penny—th-that could b-be yours.” You struggled.

“You r-r-really think s-so, Y/N)?” He mocked.

“Yes,” you huffed, taking the opportunity of the momentary neglecting to speak, “I do. You um… came quite a bit.”

A beat passed between the two of you before both eyes wondered until his eyes went white and he latched onto your cunt, his tongue suddenly darting between your folds and causing your hips to convulse at the sudden intrusion. 

“Oh fuck!”

Your ached you back and squeezed your thighs but his talons held them in place. The more you tensed, the further into your skin they would go. Your hands pulled on his hair some more and the pointed tips of each finger dug threateningly into your flesh, the tighter you tugged.

His tongue felt as if it were shifting inside of you, accommodating, attempting to locate _that_ spot. The warm muscle continued to grow inside of you until he reached your cervix.

“Fucking hell!” You cried. Your cunt throbbed around his tongue, having not rested before being stimulated again.

You felt him move slightly and released his hair, assuming he was going to leave you hanging, but when you looked down, you saw his jaw began to stretching inhumanly wide whilst his teeth began to shift into points.

“What the fuck are you—“

He sunk his top set into your pubis, interrupting you, forcing you to call out. Then you realised, it should hurt more than that. Or maybe adrenaline is masking the pain. You glanced back at the white eyes monster whose teeth had sunk in enough to draw blood but not enough to inflict too much damage

The tongue inside you stroked your walls and twirled around, dancing to locate that sweet spot. You jumped at the addition of a second tongue which circled your clit and found yourself grinding into his mouth, against both tongues, pushing one deeper into you and the other forcing you to grant more friction.

The second tongue circled against the bundle of nerves that were quickly forming until he finally found your sweet spot with his other tongue. “Oh god, yes! Right there! Please, don’t stop!” A hand released you thigh and reached for a breast, the bud rolling around between his two fingers whilst the tips of his talons slightly dug into you. You squirmed and mewled against both tongues— the feeling indescribable.

Now that you had a leg free, you hooked it over his shoulder and dug your ankle into his back as your body tensed around him. Your bare skin rubbed against the stitching of his costume as your leg stretched and locked continuously.

You weren’t sure if it could see you when both eyes disappeared the way it did, but not knowing was part of the mystery—part of what made this hot.

The tongue inside your cunt rubbed against your sweet spot as his second tongue swirled around the bundle of nerves. The talons on your breast dug in just a little bit deeper as did the others gripping your thigh. That feeling you knew all-too-well came back, the tourniquet tightening—the knot constricting your abdomen, you arched your back and closed your eyes until the tourniquet snapped off and warmth spread through your nerves, more curse words left your lips as it remained inside of you, allowing you to ride out your third orgasm through his mouth.

Like the others, it took a while for you to come back down from your high. And when you eventually opened your eyes and looked down at the Penny, his teeth were no longer in you and neither were his tongues. His teeth had retracted and his eyes were back and focusing on you, watching and observing your orgasm with a self-satisfied-sharks-tooth grin.

You caught your breath and swallowed the dry lump that had formed in your throat once again, you attempted to speak, but when you did, a series of ‘ums’ only formed. Noting your flabbergasted dictionary, it chuckled to itself before shifting to lie next to you.

You turned to face it, marvelled by it.

“Don’t you want your balloon?” he grinned and you turned to see a red balloon floating by your bed as if it had been there the whole time. You noticed something written on the balloon and tugged on the string to read it. On it read:

_You’re my fun-filled little lollipop _

You turned to face him but he was gone.

Even the smell of him was gone. Fortunately for you, you were no longer scared or wanted to run from that feeling of being watched—now that you knew who it was. Some nights, when it could smell that you needed it, it would be there. Sometimes, however, it came of its own accord. The carnal relationship you shared with it was nothing more than what it was. But sometimes, when you were both caught up in whatever it was you were doping, it would leave you a balloon in your room to come home to with written messages on it, messages in blood which dripped upwards. To let you know it hadn’t forgotten about you. 

**Author's Note:**

> Thanks for sticking around this long, hope you liked :) 
> 
> I have moderated the comments for hate only, feel free to judge. ;_;  
JustDon'tBeTooMeanPleaseI'mSensitive


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